Squalane is widely used in preparation of many cosmetics including creams, especially nutrient creams and medicated creams, milky lotion, toilet lotion, lipstick, foundation, and face powder. In addition, squalane is used as a fatting agent for high quality soap, and also used for producing medical and pharmaceutical preparations such as ointments, suppositories and medical lubricating agents. Squalene is present in the bodies of all fish, and may be extracted, for example, from the liver oil of deep-sea shark. Squalene can also be extracted in a multi-step process from vegetable oils, such as olive oil. Squalane can be produced by hydrogenating squalene from fish or vegetable oils. Squalane may be produced synthetically, for example, by the coupling of two molecules of geranyl acetone with diacetylene, followed by dehydration and complete hydrogenation; or by the dimerization of dehydronerolidol, followed by dehydration and hydrogenation.
U.S. Pat. No. 3,794,692, U.S. Pat. No. 3,859,374 and Akutagawa et al. in Bulletin of the Chemical Society of Japan, v.51(4), p. 1158-62 (1978) reported dimerization of farnesene and hydrogenation of the linear dimer to form squalane. However, as is described in detail herein, the '692 and '374 patents do not provide sufficient information to demonstrate that squalane was in fact prepared. NMR data reported in Akutagawa et al. for β-farnesene are inconsistent with that of β-farnesene known to be >97% pure, and NMR data reported in Akutagawa et al. for their linear dimer are inconsistent with the structure put forth for that linear dimer.
International Patent Publication No. WO 2010/042208 entitled “Farnesene dimers and/or farnesane dimers and compositions thereof” and filed Oct. 9, 2009 describes certain dimers and hydrogenated dimers of β-farnesene, including squalane.
Despite previous efforts to produce squalane that have been reported in the literature, there exists a need for renewable sources of squalane. There exists a continuing need for cost-effective methods for preparing squalane (e.g., high purity squalane) on large scales. There exists a need for methods that allow control of relative amounts of squalane and isomers of squalane, such isosqualane. There exists a need for squalane as well as for isosqualane that can be manufactured on large scale for use in, for example, the lubricants industry or in the cosmetic industry.